SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS
Cryptocarya is one of the genus in Lauraceae family that contains compounds having biological activities that are useful for humans. In Indonesia, Cryptocarya can be found in the eastern part of the tropical forests and known locally as "medang-medangan". Alkaloids, pyrons and flavonoids a...
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id-itb.:340852019-02-04T09:01:10ZSECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS Megawati Kimia Indonesia Theses Cryptocarya nitens, pyron, cryptofolione, deacetylcryptocaryalactone, murine leukemia P-388 cells INSTITUT TEKNOLOGI BANDUNG https://digilib.itb.ac.id/gdl/view/34085 Cryptocarya is one of the genus in Lauraceae family that contains compounds having biological activities that are useful for humans. In Indonesia, Cryptocarya can be found in the eastern part of the tropical forests and known locally as "medang-medangan". Alkaloids, pyrons and flavonoids are the main secondary metabolites in Cryptocarya genus. Some secondary metabolites from Cryptocarya showed diverse biological activities such as anticancer, anti-malarial, anti- inflammatory and antimicrobial and antiprotozoal. About 26 species of Indonesian Cryptocarya have been for their secondary metabolites and some of them were very active several cancer cells lines. One of Cryptocarya species growing in Indonesia is C. nitens. Previous research has been conducted on the stem bark of C. nitens and one compound namely yangambin, lignan type, has been obtained. However, the phytocemical study on leaves of C. nitens has not been reported yet. Therefore, the isolation of secondary metabolites from C. nitens leaves and cytotoxic assay against murine leukemia P-388 cells have been carried out. Isolation of secondary metabolites from C. nitens leaves involved several steps, including extraction at room temperature (macerated) using MeOH, chlorophyl separation by using MeOH : water (1:1) followed by partition using EtOAc. The EtOAc exctract was fractionated and purified using various chromatography techniques, such as vacuum liquid chromatography, gravity column chromatography and radial chromatography. Three pyrone derivatives were isolated from C. nitens leaves. Based on spectroscopy data including NMR (1H, 13C, HSQC, HMBC, and 1H-1H COSY), mass spectroscopy, UV-Vis spectroscopy, IR spectroscopy and also optical rotation, the compounds were identified as cryptofolione, deacetycryptocaryalactone and CN-2 compound that each has an alkyl-aryl side chain. Cryptofolione and deacetylcryptocaryalactone were reported for the first time reported from Cryptocarya leaves, particularly Indonesian Cryptocarya. However, cryptofolione has been found in C. alba fruits and stem barks of C. latifolia, C. liebertiana and C. moschata. Meanwhile, deacetylcryptocaryalactone has been isolated from stem barks of C. bourdilloni, C. liebertiana, C. moschata and C. wyliei. Bioactivity assay against murine leukemia P-388 cells showed that MeOH extract was active, while EtOAc extract was inactive with IC50 values of 3.21 ?g/mL and 44.39 ?g/ mL, respectively. Moreover, cryptofolione was active with IC50 values of of 2.94 ?g/mL. In addition, deacetycryptocaryalactone and CN-2 were inactive with IC50 values of 6.55 ?g/mL and 6.86 ?g /mL, respectively. Based on the skeleton similarity of cryptofolione and deacetylcryptocaryalactone compounds, it can be suggested that the prolongation of carbon and the presence hydroxyl at side chain will increase the cytotoxicity against murine leukemia P-388 cells. text |
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Kimia Megawati SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
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Cryptocarya is one of the genus in Lauraceae family that contains compounds having biological activities that are useful for humans. In Indonesia, Cryptocarya can be found in the eastern part of the tropical forests and known locally as "medang-medangan". Alkaloids, pyrons and flavonoids are the main secondary metabolites in Cryptocarya genus. Some secondary metabolites from Cryptocarya showed diverse biological activities such as anticancer, anti-malarial, anti- inflammatory and antimicrobial and antiprotozoal. About 26 species of Indonesian Cryptocarya have been for their secondary metabolites and some of them were very active several cancer cells lines. One of Cryptocarya species growing in Indonesia is C. nitens. Previous research has been conducted on the stem bark of C. nitens and one compound namely yangambin, lignan type, has been obtained. However, the phytocemical study on leaves of C. nitens has not been reported yet. Therefore, the isolation of secondary metabolites from C. nitens leaves and cytotoxic assay against murine leukemia P-388 cells have been carried out.
Isolation of secondary metabolites from C. nitens leaves involved several steps, including extraction at room temperature (macerated) using MeOH, chlorophyl separation by using MeOH : water (1:1) followed by partition using EtOAc. The EtOAc exctract was fractionated and purified using various chromatography techniques, such as vacuum liquid chromatography, gravity column chromatography and radial chromatography. Three pyrone derivatives were
isolated from C. nitens leaves. Based on spectroscopy data including NMR (1H,
13C, HSQC, HMBC, and 1H-1H COSY), mass spectroscopy, UV-Vis spectroscopy, IR spectroscopy and also optical rotation, the compounds were identified as cryptofolione, deacetycryptocaryalactone and CN-2 compound that each has an alkyl-aryl side chain. Cryptofolione and deacetylcryptocaryalactone
were reported for the first time reported from Cryptocarya leaves, particularly Indonesian Cryptocarya. However, cryptofolione has been found in C. alba fruits and stem barks of C. latifolia, C. liebertiana and C. moschata. Meanwhile, deacetylcryptocaryalactone has been isolated from stem barks of C. bourdilloni, C. liebertiana, C. moschata and C. wyliei. Bioactivity assay against murine leukemia P-388 cells showed that MeOH extract was active, while EtOAc extract was inactive with IC50 values of 3.21 ?g/mL and 44.39 ?g/ mL, respectively. Moreover, cryptofolione was active with IC50 values of of 2.94 ?g/mL. In addition, deacetycryptocaryalactone and CN-2 were inactive with IC50 values of
6.55 ?g/mL and 6.86 ?g /mL, respectively. Based on the skeleton similarity of
cryptofolione and deacetylcryptocaryalactone compounds, it can be suggested that the prolongation of carbon and the presence hydroxyl at side chain will increase the cytotoxicity against murine leukemia P-388 cells.
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title |
SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
title_short |
SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
title_full |
SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
title_fullStr |
SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
title_full_unstemmed |
SECONDARY METABOLITES FROM LEAVES OF CRYPTOCARYA NITENS (LAURACEAE) AND THEIR BIOACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS |
title_sort |
secondary metabolites from leaves of cryptocarya nitens (lauraceae) and their bioactivity against murine leukemia p-388 cells |
url |
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